Guided Tour: Beacon Hill

26 Charles St, Boston, MA 02114 (map)

The stylish, Italian-accented modern plates are only upstaged by the setting: Corks irregularly tiling one wall, suspended wine bottles from the ceiling and a huge pane window for spying on Charles Street passersby. Pair housemade pasta with wine of your choice, though there's a Bin 26 House Label if you so please.

25 Charles St, Boston, MA 02114 (map)

Among the numerous fancy restaurants dotting this stretch, Beacon Hill Bistro manages to straddle the fine line between locally homey and elegantly upscale. Chef James Bond's modern New England twist on French bistro fare--from farm-egg tagliatelle with fresh Maine crab to Hu-Kwa tea cured duck magret--is refreshing indulgence.

9 Bowdoin St, Boston, MA 02114 (map)

There must be a spot where state representatives, Suffolk students and downtown laborers collectively let down their hair, right? Red Hat serves that very dive-y purpose, with cheap wings and beer on tap at this century-old bar. Whatever you're escaping, this is the escape--plus trivia night, of course.

11 Charles St, Boston, MA 02114 (map)

At the original location of this historical market (with another branch on Newbury Street), Deluca's explodes with sidewalk produce displays and flowers nodding toward its iconic burgundy awning. A haute gourmet shop as much as a grocery, this is where you'll get your Bordeaux, Bucheron and Raisin Bran alike.

143 Charles St, Boston, MA 02114 (map)

Drawing in booze geeks from all over the city, this neighborhood liquor store doles out more than the usual fare. A wall of 100-plus single-malt Scotches, for one, and more than 800 varieties of fine wines and beers distinguish the highly browseable shelves. Regular tastings and genial service make bottle shopping a pleasure.

149 Charles St, Boston, MA 02114 (map)

You think there's no room on this posh avenue for down-and-dirty debauchery? Think again. The Beacon Hill Pub keeps it astoundingly real with classic dive persuasions, from cheap drinks to sticky floors to wanton dart games. A fierce and oddly attractive reality check.

20 Charles St, Boston, MA 02114 (map)

Though the first of many of the local pizza chain's multiple locations, the Beacon Hill stopover for freshly made pies and hearty gourmet toppings stands out. A dramatic, geometric metal sculpture forms the ceiling and walls, a modern touch juxtaposed against the human labor of dough rolling and sauce ladling.

33 Charles St, Boston, MA 02114 (map)

A hop-skip-jump from the Public Gardens, the independently owned Beauty Mark makes cosmetic shopping convenient. The tidy space holds only the most carefully curated items, from Kai fragrances to Julie Hewett lip color. Fittingly on gas-lit Charles Street, it's a modern twist on the neighborhood apothecary of yore.